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Have Donald Trump become the presidential nominee for the Democratic Party (preferably in a scenario where the Democratic Party has the same or similar ideology as IOTL) in any year and win the general election. The PoD can be at any point, although later ones would be more interesting.

Trump has changed his political affiliation and positions an number of times - his 2000 presidential campaign platform, which included universal healthcare, in particular was relatively liberal - and one of the few issues that he's been consistent on is opposition to free trade, which has traditionally been a Democratic stance. However, for as long as he's been a public figure, he's been dogged with allegations of sexism, racism, and unethical business practices, things that wouldn't exactly help you in a Democratic Primary.

In this scenario, he would probably need to gain some political experience (I don't see the Democrats as being that willing to nominate a businessperson who had never held political office; having him be a Democratic Governor of New York would certainly boost his credentials) and you would also need to find a way for the Democrats to be in a situation where they would nominate a centrist populist and ignore Trump's past controversies.
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